Highly Enantioselective Regiodivergent Allylic Alkylations of MBH Carbonates with Phthalides
Journal of the American Chemical Society2012Vol. 134(24), pp. 10222–10227
Citations Over TimeTop 1% of 2012 papers
Abstract
Phthalides were used for the first time in the allylic alkylation reactions with MBH carbonates for the creation of chiral 3,3-disubstituted phthalides. Highly enantioselective regiodivergent synthesis of γ-selective or β-selective allylic alkylation products was achieved by employing bifunctional chiral phosphines or multifunctional tertiary amine-thioureas as the catalyst, respectively. It was demonstrated that proper selection of catalysts and reaction conditions would differentiate an S(N)2'-S(N)2' pathway and an addition-elimination process, yielding different regioisomers of the allylic alkylation products in a highly enantiomerically pure form.
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